Ethanethiol → HCID 70977846, compound

Reaction equation

[H-].[Na+].[CH2:3]([SH:5])[CH3:4].CS(O[CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1)(=O)=O>CN(C)C=O>[Br:18][C:16]1[CH:15]=[N:14][CH:13]=[C:12]([CH2:11][S:5][CH2:3][CH3:4])[CH:17]=1

Participants

Procedure

To a cooled (0° C.) solution of sodium hydride (60% dispersion in mineral oil, 0.094 g, 2.35 mmol) in N,N-dimethylformamide (9.4 mL) was added ethanethiol (0.140 mL, 1.88 mmol). The reaction was warmed to room temperature and stirred for 30 minutes. It was then cooled to 0° C., and a solution of the title compound from Example 62 Step A (0.250 g, 0.939 mmol) in N,N-dimethylformamide (1 mL) added. The resulting solution stirred at room temperature until the reaction was complete. The reaction was then quenched with water and extracted with ethyl acetate. The combined organic extracts were washed with water and saturated aqueous sodium chloride solution, dried, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes) provided the title compound: LCMS m/z 233.91 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.50 (s, 1H), 8.39 (s, 1H), 7.79 (s, 1H), 3.62 (s, 2H), 2.39 (q, J=7.4, 2H), 1.19 (t, J=7.4, 3H).